


Backwards and Wearing High Heels

by yuletidefairy



Category: Boston Legal
Genre: Crossdressing, M/M, Yuletide 2008
Language: English
Status: Completed
Published: 2008-12-25
Updated: 2008-12-25
Packaged: 2017-10-11 20:45:58
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,201
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/116916
Author URL: https://archiveofourown.org/users/yuletidefairy/pseuds/yuletidefairy
Summary: <blockquote class="userstuff">
              <p>"Anything Denny Crane can do, I can do backwards and wearing high heels."</p>
            </blockquote>





	Backwards and Wearing High Heels

**Author's Note:**

  * For [Amy](https://archiveofourown.org/users/Amy/gifts).



"Have you heard a word I've said?" asked Brad.

"I'm sorry," said Shirley, "I'm a little distracted by the incident waiting to happen who's walking up behind you."

Alan Shore, Shirley thought, made a surprisingly nice-looking woman. The breasts were a little large but, in her experience, cross-dressers did tend to overemphasize their feminine features. Honestly, Shirley was amazed Alan had fit them into her top. He clearly had no plans to attempt to button her jacket over them, either.

Brad's expression was one of horrified disgust. Alan's was one of pleasant smugness. Shirley hoped she was maintaining her pained smile with relative grace.

"Good morning," said Alan, voice modulated in a parody of femininity.

"You sound like a phone-sex operator," Shirley said.

"Some of my favorite women are phone-sex operators," Alan retorted.

"What the _hell_ ," Brad said.

"Well, Brad," said Alan, "I'm dressed in women's clothing."

"You're dressed in _my_ clothing," said Shirley, pained smile still affixed. "When did you break into my office to steal my spare outfit? How did you break into my office?" Alan opened his mouth, and Shirley thought better of the question. "Wait. Never mind. I don't want to know."

"But why?" Brad demanded of Alan.

"Why did I break into Shirley's office?" Alan said. "I should think that would be obvious."

"Why are _wearing her clothes?_ " Brad demanded.

"Ah," said Alan. He stepped toward Brad, shifting his briefcase to one hand and straightening his shoulders. He stood taller than Brad in his--Shirley glanced down--four-inch heels. "You see, I wanted the psychological boost that only women's footwear can provide, and while I'm perfectly happy to wear a suit with pumps, I've found that some employers feel it doesn't meet the dress code. But certainly," he added, turning to Shirley with a nod, "you can't fault me for wearing something you'd wear yourself."

Shirley's face felt stretched from keeping the smile on. She thought of several replies listing all the things she could fault Alan for, including breaking, entering, and theft. She refrained because Denny was coming up the hallway and his reaction was going to be more of a punishment than Shirley could inflict. "No, you look very nice," she said.

"He," said Brad, and failed to come up with the rest of the sentence. Shirley patted his arm.

"Well, hello there." Denny had arrived. "Denny Crane. Who's representing you? I'm better."

"I work here," Alan said calmly, perfectly prepared for Denny's lapses and lewdness. "Don't you recognize me, Denny?"

Denny hesitated for only a fraction of a second. "New girl! Of course. Has anyone given you a tour yet?"

"Denny," Shirley said, "this is Al--"

"--ly," Alan said. "Ally."

"And I'm sure if you work here long enough, I'll care," Denny said.

"I'd love that tour, if you have time now," Alan said, ignoring the slight and leaning in Denny's direction.

"And why wouldn't you?" Denny said. He spread his hands to indicate his own grandeur and said, "Denny Crane."

"Yes, I know," Alan said, in that way he had, when Denny was around, that sounded dismissive and fond all at once.

Denny put his arm around Alan's waist and led him away. "Conference room over there, break room--" His hand had slid down to Alan's ass. Alan kept walking along beside him, ass swaying. "And up this way, the most important room in the whole building."

"Oh?"

"My office."

"What just happened?" Brad said.

"Alan Shore finally figured out how to get Denny to have sex with him," said Shirley, letting her expression fall to more honest dismay. "How did I not see this coming? They've been dancing around Denny's fear of dick for years."

"Are you sure it's not just some elaborate practical joke?" Brad pleaded.

"With those two? Who knows," said Shirley. "What were you saying about the case?"

"I," Brad said. "I can't remember."

"Great," said Shirley. "And now mad cow disease is contagious. I've got to go warn Paul; drop by my office when you're ready with the cross."

* * *

Alan had enjoyed an agreeable tour with Denny, but at last had had to beg off to actually do some work. His secretary seemed torn between being tickled and baffled, but when Alan settled into his work and issued firm directives, she brought him what he asked with only a few dozen blushing glances. Alan had to meet with two clients, but he assured them he'd lost a bet and would be appropriately attired in court, and didn't lose either them.

Later on, he ducked into the men's room, only to find Denny at the sink. "Oh, ho," Denny chortled, "you followed me in here, you ravishing giantess!"

"No, I'm afraid not," Alan said, "I only heard the fixtures were nicer in here."

"That suit was settled," Denny said with startling clarity of memory.

"Which says nothing of the facts of the case," Alan replied, running his finger along a faucet.

"How 'bout I show you a stall?" Denny asked, putting his hand over Alan's.

"How about I check that out privately, Denny," Alan said regretfully.

"You could check out _my_ fixtures," Denny offered, pulling Alan's hand to his crotch.

Alan rubbed lightly for a moment, until Denny's grip relaxed, and then Alan withdrew his hand. "I'm sorry, Denny, I really did come only to _use_ the facilities. If you'll excuse me."

He waited until he had heard Denny pretend to leave, leave, pop back in, and leave again before he came back out to wash his hands.

* * *

"She's magnificent," Denny confided. "Like an amazon. She's tall," he added in that weirdly reverent way he had for the oddest quirks of human anatomy. If Denny was anything, it was an equal opportunity lecher. "And the _jugs_ on her," he went on, cupping the air with his hands.

"I really don't think she's going to let you touch her jugs," Shirley said, with a stretched smile of long-suffering.

"She let me touch her ass," Denny said.

"I know," Shirley said. "I saw. Denny, is there a reason you're telling me all of this instead of Alan?"

"I haven't seen Alan today," Denny said, as if just realizing. "Do you think he's sick?"

"Often," Shirley sighed. "Today moreso than usual."

"Maybe it's the flu," Denny said.

* * *

That evening when Denny went out onto his balcony, Alan was waiting for him, cigar and glass in hand.

"Well, hello, gorgeous," Denny purred, pinning him where he was leaning on the rail.

"Hello, Denny," Alan murmured, shifting his legs.

"I'm expecting a friend later, but I'm sure he won't mind if you're here," Denny added seductively.

"It's me, Denny," Alan said, twisting to look at Denny. Denny gave him just enough space to turn and face him.

"Yes, it is," Denny said, sliding his hands up Alan's skirt and kneading his thighs.

Alan knocked back his scotch and said, "Oh, are we playing _this_ game?"

"We can play any game you want, sugar," Denny said.

"You'd better take me from behind, big boy," Alan said, in perhaps slightly too low a voice. He took a puff of the cigar, set it down, and added, "God, I hope the wig stays on this time."


End file.
